title: Gold(I)-catalyzed asymmetric induction of planar chirality by intramolecular nucleophilic addition to chromium-complexed alkynylarenes: asymmetric synthesis of planar chiral (1H-isochromene and 1,2-dihydroisoquinoline)chromium complexes.
abstract: Gold(I)-catalyzed asymmetric intramolecular cyclization of prochiral 1,3-dihydroxymethyl-2-alkynylbenzene or 1,3-bis(carbamate)-2-alkynylbenzene tricarbonylchromium complexes with axially chiral diphosphine ligand gave planar chiral tricarbonylchromium complexes of 1H-isochromene or 1,2-dihydroisoquinoline with high enantioselectivity. An enantiomeric excess of the planar chiral arene chromium complexes was largely affected by a combination of axially chiral diphosphine(AuCl)2 precatalysts and silver salts. In the case of 1,3-dihydroxymethyl-2-alkynylbenzene chromium complexes, a system of segphos(AuCl)2 with AgBF4 resulted in the formation of the corresponding antipode.
authors.affiliation: Kyoto Pharmaceutical University , Yamashina, Kyoto 607-8412, Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Murai
authors.forename: Yumi
authors.initials: Y
authors.lastname: Sota
authors.forename: Yuki
authors.initials: Y
authors.lastname: Onohara
authors.forename: Jun'ichi
authors.initials: J
authors.lastname: Uenishi
authors.forename: Motokazu
authors.initials: M
authors.lastname: Uemura
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002857:Chromium / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001578:Benzopyrans; D009942:Organometallic Compounds; D002857:Chromium; D006046:Gold